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Vol. 63 5.3 X 10~3 sec. under slightly different conditions.3. The use of the lead guard-mirror technique has established that free hydrogen atoms certainly comprise less than 2% of the total number of mirror-active particles produced in the photolysis of propionaldehyde and are probably completely absent. The result supports the view that the free formyl radical is stable up to temperatures of 100°.4. Propionaldehyde and acetone vapors have the same viscosity under the conditions of temperature and pressure used, and under similar conditions of illumination appear to produce approximately equal concentrations of alkyl radicals.The significance of this result in reference to the mechanism of the photolysis is discussed.5. The possibility is also discussed that there may be competing free radical decompositions in the photolysis of propionaldehyde. New York, N. Y.

Vol. 61 tetrachloride solution. In the first the reaction was interrupted after six hours and, in the second, after twelve and a half hours. Both gave acidic fractions boiling from 90-180°( 1 mm.), but no pure product was isolated. The boiling point changed continuously. The ozonization was not complete in either case. The acidic fraction amounted to 2.1 g. boiling below 100°( 1 mm.) and 3.2 g. boiling from 100-180°( 1 mm.) with some residue, when the ozonization was carried out for twelve and a half hours. The acid fraction gave no 2,4-dinitrophenylhydrazone.Preparation of A11-Dodecahydro-9-phenanthrone.-This ketone was prepared by the formic acid cyclization of dicyclohexenylacetylene.48 The ketone was fractionated to give a fraction boiling at 135-136°( 2 mm.) with the refractive index n25d 1.5296. The refractive index of the sample did not vary during distillation.Hydrogenation of An-Dodecahydro-9-phenanthrone to Tetradecahydro-9-phenanthrol.-A solution of 22.2 g. of the ketone in 120 ml. of ethyl alcohol was hydrogenated at 185°under a pressure of 100-200 atmospheres of hydrogen using Raney nickel10 as the catalyst. Four hours were required for complete reduction to the saturated alcohol. The product from the hydrogenation was filtered and the solvent distilled. The residue was fractionally distilled through a modified Widmer column.The portion boiling at 136-138°( 2 mm.) solidified to a waxy solid on standing for a few hours. The product did not give a sharp melting point and it has not been possible to purify it by recrystallization. The wide